Chiral Separation of Fluoxetine and Its Analogs with Charged Cyclodextrins by Capillary Electrophoresis

References

• De Camp , W. H. 1989 . The FDA perspective on the development of stereoisomers . Chirality , 1 : 2 – 6 .
   PubMed Web of Science ®Google Scholar
• Wong , D. T. , Bymaster , F. P. , Horng , J. S. and Molloy , B. B. 1975 . New selective inhibitor for uptake of serotonin into synaptosomes of rat brain. 3‐(p‐trifluoromethylphenoxy)‐N‐methyl‐3‐phenylpropylamine . J. Pharmacol. Exp. Ther. , 193 ( 3 ) : 804 – 811 .
   PubMed Web of Science ®Google Scholar
• Lemberger , L. , Rowe , H. and Crimichael , R. 1978 . Pharmacologic effects in man of a specific serotonin‐reuptake inhibitor . Science , 199 ( 4327 ) : 436 – 437 .
   PubMed Web of Science ®Google Scholar
• Lemberger , L. , Rowe , H. , Crimichael , R. , Crabtree , R. , Horng , J. S. , Bymaster , F. and Wong , D. 1978 . Fluoxetine, a selective serotonin uptake inhibitor . Clin. Pharmacol. Ther. , 23 ( 4 ) : 421 – 429 .
   PubMed Web of Science ®Google Scholar
• Freeman , C. P.L. and Hampson , M. 1987 . Fluoxetine as a treatment for bulimia nervosa . Int. J. Obesity , 3 : 171 – 177 .
   Google Scholar
• Jenike , M. A. , Buttolph , L. , Baer , L. , Ricciardi , J. and Holland , A. 1989 . Open trial of fluoxetine in obsessive‐compulsive disorder . Am. J. Psychiatry , 146 ( 7 ) : 909 – 911 .
   PubMed Web of Science ®Google Scholar
• Wong , D. T. , Fuller , R. W. and Robertson , D. W. 1990 . Fluoxetine and its two enantiomers as selective serotonin uptake inhibitors . Acta Pharm. Nord. , 2 ( 3 ) : 171 – 180 .
   PubMedGoogle Scholar
• Fuller , R. W. , Wong , D. T. and Robertson , D. W. 1991 . Fluoxetine, a selective inhibitor of serotonin uptake . Med. Res. Rev. , 11 ( 1 ) : 17 – 34 .
   PubMed Web of Science ®Google Scholar
• Soini , H. , Stefansson , M. , Riekkola , M. L. and Novotny , M. V. 1994 . Maltooligosaccharides as chiral selectors for the separation of pharmaceuticals by capillary electrophoresis . Anal. Chem. , 66 ( 20 ) : 3477 – 3484 .
   PubMed Web of Science ®Google Scholar
• Gotti , R. , Pomponio , R. and Cavrini , V. 2000 . Linear, neutral polysaccharides as chiral selectors in enantioresolution of basic drug racemates by capillary electrophoresis . Chromatographia , 52 ( 5–6 ) : 273 – 277 .
   Web of Science ®Google Scholar
• Desiderio , C. , Rudaz , S. , Raggi , M. A. and Fanali , S. 1999 . Enantiomeric separation of fluoxetine and norfluoxetine in plasma and serum samples with high detection sensitivity capillary electrophoresis . Electrophoresis , 20 ( 17 ) : 3432 – 3438 .
   PubMed Web of Science ®Google Scholar
• D'Hulst , A. and Verbeke , N. 1996 . Chiral analysis of basic drugs by oligosaccharide‐mediated capillary electrophoresis . J. Chromatogr. A , 735 ( 1–2 ) : 283 – 293 .
   Web of Science ®Google Scholar
• Piperaki , S. , Penn , S. G. and Goodall , D. M. 1995 . Systematic approach to treatment of enantiomeric separations in capillary electrophoresis and liquid chromatography II. A study of the enantiomeric separation of fluoxetine and norfluoxetine . J. Chromatogr. A , 700 ( 1–2 ) : 59 – 67 .
   Web of Science ®Google Scholar
• Soini , H. , Riekkola , M. L. and Novotny , M. V. 1992 . Chiral separations of basic drugs and quantitation of bupivacaine enantiomers in serum by capillary electrophoresis with modified cyclodextrin buffers . J. Chromatogr. , 608 ( 1–2 ) : 265 – 274 .
   PubMed Web of Science ®Google Scholar
• Christians , T. and Holzgrabe , U. 2001 . New single‐isomer chiral selector for capillary electrophoresis: the highly water‐soluble heptakis (2‐N, N‐dimethylcarbamoyl)‐β‐cyclodextrin . J. Chromatog. A , 911 ( 2 ) : 249 – 257 .
   PubMed Web of Science ®Google Scholar
• Hongwei , Y. , Ching , C. B. , Ping , F. and Ng , S. C. Liquid chromatographic retention behavior and enantioseparation of fluoxetine on a new β‐cyclodextrin bonded‐phase column . Adsorpt. Sci. Technol., Proc. Pac. Basin Conf. 2nd . Edited by: Do and Duong , D. pp. 144 – 148 . Singapore : World Scientific Publishing Co. Pte. Ltd. .
   Google Scholar
• Olsen , B. A. , Wirth , D. D. and Larew , J. S. 1998 . Determination of fluoxetine hydrochloride enantiomeric excess using high‐performance liquid chromatography with chiral stationary phases . J. Pharm. Biomed. Anal. , 17 ( 4–5 ) : 623 – 630 .
   PubMed Web of Science ®Google Scholar
• Piperaki , S. and Parissi‐Poulou , M. 1993 . Use of cyclodextrins as chiral selectors for direct resolution of the enantiomers of fluoxetine and its metabolite norfluoxetine by HPLC . Chirality , 5 ( 4 ) : 258 – 266 .
   Web of Science ®Google Scholar
• Chankvetadze , B. 1997 . “ Native and derivatized cyclodextrins as chiral selectors in capillary electrophoresis ” . In Capillary Electrophoresis in Chiral Analysis 141 – 228 . Chichester , , UK : John Wiley & Sons .
   Google Scholar
• Terabe , S. 1989 . Electrokinetic chromatography: an interface between electrophoresis and chromatography . Trends Anal. Chem. , 8 ( 4 ) : 129
   Web of Science ®Google Scholar
• Fanali , S. 1989 . Separation of optical isomers by capillary zone electrophoresis based on host–guest complexation with cyclodextrins . J. Chromatogr. , 474 ( 2 ) : 441 – 446 .
   Web of Science ®Google Scholar
• Chankvetadze , B. , Endresz , G. and Blaschke , G. 1994 . About some aspects of the use of charged cyclodextrins for capillary electrophoresis enantioseparation . Electrophoresis , 15 : 804 – 807 .
   PubMed Web of Science ®Google Scholar
• Chankvetadze , B. , Endresz , G. , Bergenthal , D. and Blaschke , G. 1995 . Enantioseparation of mianserine analogues using capillary electrophoresis with neutral and charged cyclodextrin buffer modifiers 13C NMR study of the chiral recognition mechanism . J. Chromatogr. A , 717 ( 1–2 ) : 245 – 253 .
   Web of Science ®Google Scholar
• Tait , R. J. , Thompson , D. O. and Stobaugh , J. F. 1994 . Sulfobutyl ether β‐cyclodextrin as a chiral discriminator for use with capillary electrophoresis . Anal. Chem. , 66 ( 22 ) : 4013 – 4018 .
   Web of Science ®Google Scholar
• Vincent , J. B. , Sokolowski , A. D. , Nguyen , T. V. and Vigh , G. 1997 . A family of single‐isomer chiral resolving agents for capillary electrophoresis. 1. Heptakis(2,3‐diacetyl‐6‐sulfato)‐β‐cyclodextrin . Anal. Chem. , 69 ( 20 ) : 4226 – 4233 .
   Web of Science ®Google Scholar
• Vincent , J. B. , Kirby , D. M. , Nguyen , T. V. and Vigh , G. 1997 . A family of single‐isomer chiral resolving agents for capillary electrophoresis. 2. Hepta‐6‐sulfato‐β‐cyclodextrin . Anal. Chem. , 69 ( 21 ) : 4419 – 4428 .
   PubMed Web of Science ®Google Scholar
• Cai , H. , Nguyen , T. V. and Vigh , G. 1998 . A family of single‐isomer chiral resolving agents for capillary electrophoresis. 3. Heptakis(2,3‐dimethyl‐6‐sulfato)‐β‐cyclodextrin . Anal. Chem. , 70 ( 3 ) : 580 – 589 .
   PubMed Web of Science ®Google Scholar
• Zhou , L. , Johnson , B. D. , Miller , C. and Wyvratt , J. M. 2000 . Chiral capillary electrophoretic analysis of the enantiomeric purity of a pharmaceutical compound using sulfated β‐cyclodextrin . J. Chromatogr. A , 875 ( 1–2 ) : 389 – 401 .
   PubMed Web of Science ®Google Scholar
• Cladrowa‐Runge , S. , Hirz , R. , Kenndler , E. and Rizzi , A. 1995 . Enantiomeric separation of amphetamine related drugs by capillary zone electrophoresis using native and derivatized β‐cyclodextrin as chiral additives. , 710 ( 2 ) : 339 – 345 .
   Google Scholar
• Wozniak , T. J. , Bopp , R. J. and Jensen , E. C. 1991 . Chiral drugs: an industrial analytical perspective . J. Pharm. Biomed. Anal. , 9 ( 5 ) : 363 – 382 .
   PubMed Web of Science ®Google Scholar